a professional card player who makes a living by cheating at card games
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a pen with indelible ink that will write on any surface
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a shallow-draft sailboat with a sharp prow, flat bottom, and triangular sail; formerly used along the northern Atlantic coast of the United States
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Sharpie \Sharp"ie\, n. (Naut.) A long, sharp, flat-bottomed boat, with one or two masts carrying a triangular sail. They are often called {Fair Haven sharpies}, after the place on the coast of Connecticut where they originated. [Local, U.S.]